1-(3-oxopent-1-en-4-ynyl)-6-(oxoprop-2-ynyl)cyclohepta-1,3,5-triene | 156836-25-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3-oxopent-1-en-4-ynyl)-6-(oxoprop-2-ynyl)cyclohepta-1,3,5-triene
• 英文别名: 1-(3-oxopent-1-en-4-ynyl)-6-(1-oxoprop-2-ynyl)cyclohepta-1,3,5-triene；(E)-1-(6-prop-2-ynoylcyclohepta-1,3,5-trien-1-yl)pent-1-en-4-yn-3-one
• CAS: 156836-25-8
• 化学式: C₁₅H₁₀O₂
• 分子量: 222.243
• InChiKey: QZHCMLJFZRNOMW-MDZDMXLPSA-N

物化性质

• 沸点：
  376.9±52.0 °C(predicted)
• 密度：
  1.225±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(3-oxopent-1-en-4-ynyl)-6-(oxoprop-2-ynyl)cyclohepta-1,3,5-triene 以4%的产率得到
  参考文献：
  名称：

  Higuchi Hiroyuki, Sakon Chiaki, Asano Kaori, Ojima Juro, Iyoda Masahiko, +, J. Chem. Soc. Perkin Trans. 1, (1994) N 20, S 2915-2920

  摘要：

  DOI：
• 作为产物：
  描述：

  1-formyl-6-(2-formylvinyl)cyclohepta-1,3,5-triene 在 barium permanganate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 1-(3-oxopent-1-en-4-ynyl)-6-(oxoprop-2-ynyl)cyclohepta-1,3,5-triene
  参考文献：
  名称：

  Syntheses and properties of methano-bridged dichlorodidehydro-[16]-, -[20]-and-[24]-annulenediones

  摘要：

  Bisethynylation of the vinylogous dialdehydes of cyclohepta-1.3,5-triene-1,6-dicarbaldehyde with ethynylmagnesium bromide followed by oxidation of the resulted diols afforded the diacetylenic diketones. Intramolecular oxidative coupling of these diketones under the Glaser conditions unexpectedly afforded three annulenediones with a 1,4-dichlorobutatriene moiety. The unusual structures were confirmed by X-ray crystallographic analysis of 10,13-dichloro-11.12-didehydro-1,6methano[16]annulene-9,1 4-dione. These annulenediones exhibited strong diatropicity in D2SO4 due to the dicationic 14 pi-, 18 pi- and 22 pi-electron species and their diatropicities were shown to increase with increasing ring size.

  DOI：

  10.1039/p19940001453

文献信息

• Higuchi Hiroyuki, Asano Kaori, Ojima Juro, Yamamoto Koji, Yoshida Toshika+, J. Chem. Soc. Perkin Trans. 1, (1994) N 11, S 1453-1468
  作者：Higuchi Hiroyuki, Asano Kaori, Ojima Juro, Yamamoto Koji, Yoshida Toshika+

  DOI：——

  日期：——
• Higuchi Hiroyuki, Sakon Chiaki, Asano Kaori, Ojima Juro, Iyoda Masahiko, +, J. Chem. Soc. Perkin Trans. 1, (1994) N 20, S 2915-2920
  作者：Higuchi Hiroyuki, Sakon Chiaki, Asano Kaori, Ojima Juro, Iyoda Masahiko, +

  DOI：——

  日期：——
• Higuchi, Hiroyuki; Sakon, Chiaki; Asano, Kaori, Journal of the Chemical Society. Perkin transactions I, 1994, # 20, p. 2915 - 2920
  作者：Higuchi, Hiroyuki、Sakon, Chiaki、Asano, Kaori、Ojima, Juro、Iyoda, Masahiko、et al.

  DOI：——

  日期：——
• Syntheses and properties of methano-bridged dichlorodidehydro-[16]-, -[20]-and-[24]-annulenediones
  作者：Hiroyuki Higuchi、Kaori Asano、J?ro Ojima、Koji Yamamoto、Toshikatsu Yoshida、Tomohiro Adachi、Gaku Yamamoto

  DOI：10.1039/p19940001453

  日期：——

  Bisethynylation of the vinylogous dialdehydes of cyclohepta-1.3,5-triene-1,6-dicarbaldehyde with ethynylmagnesium bromide followed by oxidation of the resulted diols afforded the diacetylenic diketones. Intramolecular oxidative coupling of these diketones under the Glaser conditions unexpectedly afforded three annulenediones with a 1,4-dichlorobutatriene moiety. The unusual structures were confirmed by X-ray crystallographic analysis of 10,13-dichloro-11.12-didehydro-1,6methano[16]annulene-9,1 4-dione. These annulenediones exhibited strong diatropicity in D2SO4 due to the dicationic 14 pi-, 18 pi- and 22 pi-electron species and their diatropicities were shown to increase with increasing ring size.